


Never Regret a Thing

by LivingLiza



Category: Arrow (TV 2012)
Genre: F/M
Language: English
Status: Completed
Published: 2016-10-22
Updated: 2016-11-25
Packaged: 2018-08-24 00:00:00
Rating: Mature
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 2
Words: 2,463
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/8347933
Author URL: https://archiveofourown.org/users/LivingLiza/pseuds/LivingLiza
Summary: After going through a rough breakup, Felicity Smoak decided to do something wild. What if her "something wild" turned out to be her boss, Oliver Queen? Originally posted on FanFiction.net, but I got a suggestion to also post it here.





	1. Chapter 1

Hey everybody! Hope you’re all doing great and feeling great. This is my first attempt at this type of story so let me know how it is! 

 

She never expected this. Felicity Smoak was a good girl. She had graduated high school, went to college at MIT, met a nice boy, got a good job at Queen Consolidated, volunteered on weekends. All of that was true, apart from the nice boy. She had just thrown the last of his clothing put of the window of their apartment in Starling City. Well, her apartment. After this liberating experience she called up her best friend Nadine with one purpose; she wanted to get drunk off her ass. She and Nadine made their way to Verdant, an upscale club in the Glades.  
And drink she did. She wasn’t just drunk on the alcohol. She was drunk on the feeling of being liberated from a shitty relationship. She was flying on a cloud, captured in a haze of anxiety and joy.  
“I don’t know about you Nadine,” Felicity slurred. “But I think I need another shot of tequila!”  
“Make that two Lis.”  
“Will do.”  
Felicity picked her way towards the bar, eagerly meeting the gazes of all the men trailing her with their eyes. She reached the bar and motioned to the bartender to give her two shots of tequila. While she was waiting for her drinks she felt one pair of eyes burning into her like none of the others. She turned her eyes to meet his gaze, and although she only meant to glance for a second, her eyes lingered.   
He was beautiful. Six feet tall, with piercing blue eyes and close cropped blonde hair, and muscles like a god. She caught his eye, and raised an eyebrow, as if she was challenging him. Asking him to come over and talk to her. And that he did.  
“What’s a girl like you doing all alone in a bar on a Friday night?” He asked.  
“What’s a guy like you doing using a shit pickup line like that?” She responded. He chuckled, coming a little closer and leaning against the bar.  
“I suppose your right,” he said, “but that was my not so subtle way of asking if your taken.”  
“Well, I’m not. And I think I know your next question.”  
“And what is that?”  
“My name. It’s Felicity by the way.”  
“Well, Felicity, than you for saving me the trouble of asking. My name is Oliver.”  
“ Well, Oliver, I am very drunk. I just got out of a five year relationship and I haven’t had sex in three months. I am very horny and I just want to hook up with someone. Do you think you can handle that?”   
Oliver leaned in very close to Felicity, brushing a piece of hair away from her throat. She could feel his warm breath tickling her skin as he whispered,  
“My place or yours?”  
\-------------------------------------------------------------------------------------------------------------------------------------------  
Felicity giggled as Oliver guided her out of the club, his hand on the small of her back. He motioned with one hand to the doorman to have his car brought around, his arm never leaving her back. When the car arrived, he pulled her into backseat, pressing his lips against hers. He ran his tongue against her lips, begging for entrance, which she gladly granted him. He glided his tongue against her’s, gently at first but with more urgency as she curled her fingers into his hair, moaning. He held the back of her head tightly with one hand, while he snaked the other around her waist, clutching her tightly against him. The car came to a halt in front of a massive house. Oliver pulled Felicity out of the car by her wrist urging her gently up the stairs towards his bedroom. Once they reached the high ceilinged room Oliver pushed her against the wall, kissing her again, even more fiercely than before, his hand reaching behind her and beginning to unzip her dress. He was moving painfully slowly, and she reached for her zipper. He pushed her hand away, and mumbled  
“We are going to do this my way.” and continued his slow pace. Much to her own surprise, his controlling words seemed to excite her. She had never really known what really turned her on because she had only been with one guy her entire life, and compared to Oliver, he was a child. Oliver was a real man and she could feel the proof pressed up against her. He continued to inch her zipper down slowly while moving his lips from her’s and letting them travel towards her neck. He sucked lightly on her pulse point, just hard enough to leave a small mark on her neck. He smirked knowing that the mark would remain on her, a symbol of what they had done. After he finished unzipping her dress, he moved the straps down over her shoulders and over her hands, until it hung around her hips. He then lifted both her hands over her head, holding them in place with one of his own. He then forced the rest of her dress over her hips, leaving her clad only in her bra and panties. He then picked her up and threw her onto the bed. He climbed on top of her and kissed her fiercely while he deftly unhooked her bra, throwing it to the side. He moved his mouth towards her right breast, covering her nipple with his mouth, while massaging the other one with his hand. Felicity moaned out his name with pleasure, raking her fingers through his hair and down his back. He moved his hand toward the nipple, rubbing it roughly until it tightened. He then began kissing down her stomach. She lifted her hips so he could slide her panties over them, scraping her slightly with his fingers as he went. He then pushed her legs apart so her knees touched the mattress. He lowered his mouth and ran his tongue over her clit, nipping lightly with his teeth. Felicity squirmed under him, groaning with pleasure as he inserted one finger inside her, and then two. As he pumped his fingers up and down. She felt heat pooling in her stomach and as she reached her orgasm she screamed out Oliver’s name. He then pulled his fingers out of her rolled a condom over himself and then inserted himself into her and moved himself quickly in and out of her. When he reached his climax, he pulled out of her and lay down next to her. They both dozed off, and not until the morning would Felicity realize what she had done. She had slept with her boss.

Hope you liked it! I’ll try to update soon. I don’t really know where this story is going but I’m open to suggestions. Byeeee!


	2. Chapter 2

**Summary for the Chapter:**

> What happens the after a one night stand?

The sun was shining through large windows in a bedroom. Felicity would normally enjoy this natural light, but right now she was doing anything but enjoying this light. Her head was pounding and felt like it weighed a million pounds. She stretched out her legs and pulled herself into a sitting position, rubbing her eyes. She looked over to the other side of the bed to see who was there, because, embarrassingly, she couldn't remember his name or what he looked like. To be completely honest, she was thankful she wouldn't have to interact with him. She hurriedly climbed out of bed hoping to keep up this lack of conscious communication. She picked up her clothes, sliding on her dress and pulling her phone out of the pocket. Thankfully, it wasn't completely dead. Felicity used her little remaining battery power to call an Uber, and dashed outside to meet her car.

Uber, she thought, was probably the most useful invention ever. It made the walk of shame infinitely less embarrassing . Lucky for Felicity, it was Saturday and she wouldn't have to go to work. She was looking forward to taking two days to herself. Well, mostly to herself. She would still volunteer Sunday morning at a kids’ center in the Glades. But today, Saturday, was a day ti wallow in self pity. She baked chocolate chip muffins and binge ate them while watching CSI and using fancy-smelling face masks. Monday morning came all to quickly for Felicity’s taste. She hauled herself out of bed and began to prepare breakfast for herself. After eating her breakfast she climbed into her car and drove by her friend Nadine’s house in order to pick her up for work. “Good morning Nadine!” She called, honking the car’s horn.

“Hurry up! We’re going to be late!”

“Since when have you cared about being on time to work?” Nadine said, flustered, nearly dropping her files.

“Since I started feeling like I need to retain one ounce of my nice normalcy.”

“Ooh. Someone is regretting her one night stand. Was he shitty in bed?”

“Nope. It definitely was not that.”

“So he was good?”

“Good doesn’t even begin to describe it. It was fan-freaking-tastic-best-sex-of-my-life-nothing-can-compare.”

“I mean, he was pretty hot.” Nadine conceded. “Did you get his number?”

“Number?” Felicity said with a short laugh. “Nadine, I don’t even remember his name.”

“Whatever. I heard we get to meet the new boss today. Apparently he's like the nephew of the old guy.”

“Cool. Maybe he’ll breathe some life into the company. It’s been a little dead around there for a while.”

Felicity parked her car in the Queen Consolidated employee lot and entered to monstrosity of a building that housed this corporation. She waved to the security guard as she did every morning, and rode her way down to the IT department, separating from Nadine, who went to the top floor, where she worked as the CFO’s assistant. She settled into her chair, preparing to work for about three hours until the meeting where they would meet the new boss. She had read in the memo that his name was Oliver Queen. For some reason, that seemed eerily familiar, but Felicity had no Idea why. She shook off this feeling, plugged in her headphones, and began to work to the smooth sounds of Tom Petty and the Heartbreakers, followed by Taylor swift. Felicity’s taste in music was somewhat eclectic, but she didn't mind. Good music is good music, she always said.

After around an hour she received a message from Nadine, telling her to come to the 32nd floor bathroom, their traditional meet up spot, about half way between their offices. As Felicity stood in the elevator on her way up to the 32nd floor, she pondered what the reason for Nadine’s urgent message was. Felicity exited the elevator and turned the corner into the bathroom. “What’s up Nadine?” Felicity asked, her voice full of concern.

“Are you okay?”

“I am,” Nadine replied, “But soon you won’t be.”

“Nadine, you’re starting to scare me.”

  “Okay, don’t freak out...”

“You probably should have led with that.”

“Shh. Don’t interrupt me. I think the new CEO might be the guy you hooked up with on Friday night.” Nadine rushed. “I’m not sure, I was pretty drunk, but it looks like him.”

“Holy shit! What am I supposed to do?”

“Ummm. I’d avoid him, unless you're dead set on jumping his bones again.”

“Very funny.”

“I’m not kidding. You were right, he is insanely hot. I mean, I can only imagine what he looks like naked.”

“Nadine. You are such a perv. He’s our boss!”

“I’m not the one who hooked up with him.”

“Ughhh. I doubt he remembers me either, we were both super drunk. Also, there is a chance it wasn’t him that I hooked up.” “Whatever stops the tears sweetie, whatever stops the tears.”

\------------------------------------------------------------------------------------------------------------

At 12:30, Felicity dragged herself up to the boardroom, preparing herself to space out through an entire meeting. The second she walked through the door of the meeting, however, the pit that had been forming in her stomach since she had spoken to Nadine grew even more. She turned her head so her hair covered her face, and hurried to the back of the boardroom, praying she wouldn’t make eye contact with anyone. As soon as she reached her chair in the corner, she whipped out her phone and began scrolling through her Facebook feed, anything to keep her mind, and eyes, off the young, tall, man with a slight stubble, standing at the front of the room.

She shook her head and turned her thoughts back too Facebook. Her feed was filled with endless photos of friends’ engagements, weddings, and even babies. The babies caused her more stress than anything else. She was, after all, only 23. She couldn't even begin too fathom marriage, let alone children. The CFO, Mr. Clement, cleared his throat and announced that the meeting was beginning. He introduced the man was Oliver Queen, the new CEO, who was the nephew of the old CEO, who had spent the last few years at business school on the east coast. Felicity chuckled and thought to herself, it’s nice to know that nepotism is alive and well. She briefly looked up and made eye contact with Oliver, Mr. Queen, and then quickly began studying her fingers. She continued to do so for the remainder of the meeting, vaguely listening to the new CEO’s grand new plans for implementing an entirely new computer system. Yay, Felicity thought, I shouldn't plan on having free time for the next few years. After the meeting was finished, Felicity practically sprinted out of the room, but skidded to a halt as she heard her name called.

“Ms. Smoak.” Mr. Clement called.

“Yes, sir.” Felicity replied as she turned around.

“I would like to personally introduce to Mr. Queen. You two will be working side by side with the introduction of the new computer system. Mr. Queen, this is Felicity Smoak, the head of the IT department.”

“It’s a pleasure to meet you Mr. Queen.” Felicity interjected before her new boss could mention that this was not, in fact, an introduction.

“It’s nice to meet you too Ms. Smoak.” He replied.

“Well, it was very nice to meet you but I am afraid that this new computer system has given me a lot of work to catch up on, as well as the fact that I need to meet with my team, so if you’ll kindly excuse me.”

“Of course Ms. Smoak.” Mr. Queen said, before Clement could even open his mouth. “I will email you to set up a meeting about the new computers sometime soon.” “Have a nice day.” Felicity said, rushing out the door.

She exhaled deeply as she entered the elevator. She thought to herself, is it possible he doesn't remember me?


End file.
